Iodine → 2-Iodo-5-(1-methylethyl)phenol

HRID 2363140Notes

Reaction equation

HRID 2363140 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[I:11]I>C(O)(=O)C>[I:11][C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][C:6]=1[OH:10]

Participants

4

Reactant 2

HCID 807IodineHCID 120593-Isopropylphenol

Product 1

HCID 534171182-Iodo-5-(1-methylethyl)phenolYield 160.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-isopropylphenol (670 mg, 4.92 mmol), KIO3 (210 mg, 0.98 mmol), and I2 (500 mg, 1.97 mmol) in acetic acid was stirred for 3 days at room temperature. The solvent was removed at reduced pressure. The residue was diluted with Et2O and washed with aq. NaHCO3, aq. Na2S2O3, and brine. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified with flash column chromatography to give the title compound (830 mg, 64%).

Workup

  1. customThe solvent was removed at reduced pressure
  2. additionThe residue was diluted with Et2O
  3. washwashed with aq. NaHCO3, aq. Na2S2O3, and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with flash column chromatography

Sources & evidence

ORD record
ord-7da086746ca54067bd2b5af74451aa64
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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